A General Direct Aldehyde C–H Alkylation via TBADT-Nickel Synergistic Catalysis

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-24 DOI:10.1021/acs.orglett.5c00949

Zhimin Hu, Ji-Wei Sang, Shize Xie, Yujia Song, Qiuhao Li, Bing Wang, Zheng-Yang Xu, Yu Zhang, Runhui Liu, Wei-Dong Zhang, Jinxin Wang

引用次数: 0

Abstract

Herein, we present a nickel/tetrabutylammonium decatungstate (TBADT)-catalyzed protocol for general C–H alkylation of aldehydes, enabling the efficient synthesis of aliphatic ketones through ligand-controlled cross-coupling. This mild and cost-effective methodology demonstrates broad substrate compatibility with various commercially available aldehydes and both activated and unactivated alkyl bromides, delivering target products in high yields. Notably, the practical utility of this catalytic system has been highlighted through a concise two-step synthesis of the commercially valuable musk odorant Aurelione from readily available starting materials.

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tbadt -镍协同催化的乙醛C-H直接烷基化研究

在此，我们提出了镍/十钨酸四丁基铵（TBADT）催化醛的一般C-H烷基化的方案，使通过配体控制的交叉偶联高效合成脂肪族酮。这种温和且具有成本效益的方法与各种市售醛以及活化和未活化的烷基溴具有广泛的底物相容性，以高收率提供目标产品。值得注意的是，该催化系统的实际用途已经通过简单的两步合成了具有商业价值的麝香气味剂Aurelione。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.